Substituted 1-pyridinyloxy-1-(imidazolyl)-2-butanone compounds and their use as fungicides

ABSTRACT

Substituted 1-pyridinyloxy-1-(triazolyl or imidazolyl)-2-butanone compounds which correspond to the formula: ##STR1## wherein each X independently represents halogen, methyl, trichloromethyl, trifluoromethyl, or cyano; n represents an integer of 0 to 3; Y represents --N or --CH; and R represents methyl, methoxy, or ethoxy are prepared. These compounds have been found to exhibit a high degree of fungicidal activity, and compositions containing said compounds are so employed.

CROSS REFERENCE TO RELATED APPLICATIONS

This is a divisional of application Ser. No. 956,957 filed Nov. 2, 1978.

DESCRIPTION OF PRIOR ART

1-Phenoxy-1-(1,2,4-triazol-1-yl)-2-alkanone compounds and derivativeshaving fungicidal activity are disclosed in German Offen. 2,201,063(Chemical Abstracts 79, 105257y (1973)) and German Offen. 2,247,186(Chemical Abstracts 80, 146129k (1974)).

SUMMARY OF THE INVENTION

The present invention is directed to novel substituted1-pyridinyloxy-1-(triazolyl or imidazolyl)-2-butanone compounds, tocompositions containing said active compounds, and to the use of suchcompositions for control of fungi that attack plants. The compounds ofthe present invention correspond to the formula ##STR2## wherein each Xindependently represents halogen, methyl, trichloromethyl,trifluoromethyl, or cyano; n represents an integer of 0 to 3; Yrepresents --N or --CH; and R represents methyl, methoxy, or ethoxy.

In the present specification and claims, the term "halogen" is employedto designate chloro, fluoro, or bromo.

The compounds of the invention are solids at ambient temperatures andare of low mammalian toxicity. The compounds are substantially insolublein water and usually are moderately to highly soluble in common organicsolvents.

The compounds of the present invention can be prepared by the reactionof substantially equimolar amounts of 1H-1,2,4-triazole or imidazolewith an appropriate 1-halo-1-pyridinyloxy-1,1-dimethyl-2-butanonecompound corresponding to the formula ##STR3## wherein X, n, and R areas defined hereinabove, and Z is bromo or chloro. The reaction iscarried out in presence of a solvent and a hydrogen halide acceptor.Preferably, the reaction is carried out at a temperature within therange of from -10° to 110° C., most preferably from 0° to 35° C.

Suitable solvents useful in carrying out the reaction include acetone,acetonitrile, halogenated hydrocarbon solvents such as methylenechloride, and hydrocarbon solvents such as hexane, benzene, or toluene.Suitable hydrogen halide acceptors useful in carrying out the reactioninclude conventional bases, such as potassium or sodium carbonate,triethylamine and 1,5-diaza(5.4.0)undec-5-ene as is well known to thoseskilled in the art.

The product of the reaction can be purified as desired using well knownprocedures, such as recrystallization from a solvent.

DESCRIPTION OF SOME PREFERRED EMBODIMENTS

The following examples illustrate the present invention and the mannerby which it can be practiced, but as such, should not be construed aslimitations on the overall scope of the same.

PREPARATION OF INTERMEDIATES EXAMPLE I1-Bromo-1-(5-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone ##STR4##

A mixture of 12.96 grams (g) (0.1 mole) of 5-chloro-2-hydroxypyridine,17.9 g (0.1 mole) of 1-bromo-3,3-dimethyl-2-butanone, and 15 g (0.054mole) of silver carbonate in hexane was stirred and heated at refluxtemperature for 48 hours. The reaction mixture was filtered, and thesolvent removed by evaporation. The residue was dissolved in methylenechloride and filtered through silica gel. Evaporation of the solventgave 10.5 g (46 percent (%) yield) of1-(5-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone. A samplerecrystallized from pentane had a melting point of 68°-69.5° C.

A mixture of 10.5 g (0.046 mole) of1-(5-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone, prepared above, and8.37 g (0.047 mole) N-bromosuccinimide (NBS) in 300 ml. carbontetrachloride, with stirring, was irradiated and heated with a sunlampuntil all of the NBS was consumed (about 45 min.). The reaction mixturewas cooled, filtered, and the filtrate washed with aqueous sodiumbisulfite and dried. After removal of the solvent, there was obtained aquantitative yield of1-bromo-1-(5-chloro-2-pyridinyl-oxy)-3,3-dimethyl-2-butanone, a lightyellow oil.

EXAMPLE II 1-Bromo-1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone##STR5##

To a stirred mixture of 400 g (3.09 moles) of 2-hydroxy-6-chloropyridineand 450 g (3.26 moles) potassium carbonate in 3000 ml acetonitrile wasadded 551 g (3.08 moles) 1-bromo-3,3-dimethyl-2-butanone. The reactionmixture was stirred at 45°-50° C. for 1.5 hours and then filtered. Thesolids were washed several times with acetonitrile, the filtrate dried(MgSO₄) and the solvent evaporated. Crystallization of the residue frompentane gave 610 g (87% yield) of1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone. A secondrecrystallization from pentane gave product melting at 43°-44.5° C.

A stirred solution of 227.68 g (1.0 mole) of1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone, prepared above, in1000 ml dioxane was heated to 65° C. The heat source was removed and175.8 g (1.1 mole) bromine added dropwise. After the addition of thebromine, the solution was stirred for 10 minutes and then poured into 3liters ice water containing 25 g sodium bisulfite. The mixture was madeslightly basic with 50% NaOH and twice extracted with 500-ml portions ofpentane. The pentane extracts were washed with 1000 ml of 5% NaOH anddried, giving 259 g (84% yield) of1-bromo-1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone.Crystallization from pentane gave a white solid melting at 50°-52° C.

EXAMPLE III1-(6-Chloro-2-pyridinyloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone##STR6##

A solution of 259 g (0.845 mole) of1-bromo-1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone in 300 mlacetone was added dropwise to a stirred solution of 58.4 g (0.845 mole)1H-1,2,4-triazole and 124.4 g (0.9 mole) potassium carbonate in 500 mlacetone. The reaction mixture was maintained at a temperature below 35°C. After the addition was complete, the mixture was stirred for 30minutes and then filtered. The solid product was washed with acetone anddried. Crystallization from 800 ml methanol and 200 ml water gave 170 g(69% yield) of1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-1-(1,2,4-thiazol-1-yl)-2-butanonemelting at 106°-107.5° C.

Elemental analysis:

    ______________________________________                                                  C        H          N                                               ______________________________________                                         Theory     52.97      5.13       19.01                                       Found       52.90      5.22       18.83                                       ______________________________________                                    

EXAMPLE IV1-(6-Fluoro-2-pyridinyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanone##STR7##

To a stirred solution of 14.5 g (0.05 mole) of1-bromo-1-(6-fluoro-2-pyridinyloxy)-3,3-dimethyl-2-butanone in 75 mlacetone cooled to -10° C. was added 3.4 g (0.05 mole) imidazole. Then,7.61 g (0.05 mole) of 1,5-diaza(5.4.0)undec-5-ene was added dropwise.After the addition was complete, the mixture was stirred for 30 minutesat 0° C. and the solvent evaporated. Water was added to the residue andthe mixture extracted with diethyl ether. The ether extract was driedusing magnesium sulfate and the solvent evaporated. Chromatography onsilica gel (8:2 hexane:acetone) gave 6.3 g (55% yield) of1-(6-fluoro-2-pyridinyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanone.Recrystallization from hexane gave product melting at 90°-93° C.

Elemental analysis:

    ______________________________________                                                  C        H          N                                               ______________________________________                                        Theory      60.64      5.82       15.15                                       Found       60.44      5.84       15.07                                       ______________________________________                                    

Using similar procedures, additional compounds of the present inventionlisted in Table 1 were prepared.

                                      TABLE 1                                     __________________________________________________________________________     ##STR8##                                                                     Oxy                      Melting                                                                             Elemental Analysis                             Example                                                                            Position                                                                           Xn    Y    R   Point ° C.                                                                     C  H  N                                      __________________________________________________________________________    V    2    5-Cl  N    CH.sub.3                                                                          97.9                                                 VI   2    3,5-Cl                                                                              N    CH.sub.3                                                                          98-100                                                                              T*                                                                              47.43                                                                            4.29                                                                             17.02                                                                 F 47.60                                                                            4.43                                                                             16.88                                  VII  2    3,5-Cl; 6-F                                                                         N    CH.sub.3                                                                          105-109                                                                             T 44.97                                                                            3.77                                                                             16.14                                                                 F 44.86                                                                            3.74                                                                             15.89                                  VIII 2    6-F   N    CH.sub.3                                                                          108-110                                                                             T 56.10                                                                            5.43                                                                             20.13                                                                 F 55.86                                                                            5.45                                                                             19.94                                  IX   2    3,5,6-F                                                                             N    CH.sub.3                                                                          104-105.5                                                                           T 49.68                                                                            4.17                                                                             17.83                                                                 F 49.53                                                                            4.17                                                                             17.65                                  X    2    3,5,6-Cl                                                                            N    CH.sub.3                                                                          127.5-129.5                                                                         T 42.94                                                                            3.60                                                                             15.41                                                                 F 42.87                                                                            3.62                                                                             15.30                                  XI   2    3,6-Cl                                                                              N    CH.sub.3                                                                          146.5-148.5                                                                         T 47.43                                                                            4.29                                                                             17.02                                                                 F 47.19                                                                            4.33                                                                             16.59                                  XII  2    5,6-Cl                                                                              N    CH.sub.3                                                                          130-133                                                                             T 47.43                                                                            4.29                                                                             17.02                                                                 F 47.51                                                                            4.29                                                                             16.87                                  XIII 2          N    CH.sub.3                                                                          80-83                                                XIV  2    5-CN  N    CH.sub.3                                                                          149-150.5                                                                           T 58.93                                                                            5.30                                                                             24.55                                                                 F 58.72                                                                            5.44                                                                             24.31                                  XV   2    6-Cl  4-CCl.sub.3 N                                                                      CH.sub.3                                                                          135-137.5                                                                           T 40.80                                                                            3.42                                                                             13.60                                                                 F 40.65                                                                            3.53                                                                             13.29                                  XVI  2    5-CF.sub.3                                                                          N    CH.sub.3                                                                          88-90 T 51.22                                                                            4.61                                                                             17.07                                                                 F 51.34                                                                            4.68                                                                             16.86                                  XVII 2    6-CH.sub.3                                                                          N    CH.sub.3                                                                          123-124.5                                                                           T 61.30                                                                            6.61                                                                             20.43                                                                 F 61.18                                                                            6.56                                                                             20.10                                  XVIII                                                                              2    6-Cl  N    OCH.sub.3                                                                         105-106                                                                             T 50.24                                                                            4.87                                                                             18.03                                                                 F 49.83                                                                            4.80                                                                             17.76                                  XIX  2    6-Cl  N    OC.sub.2 H.sub.5                                                                  114-120                                              XX   2    5-CN  CH   CH.sub.3                                                                          176- 178                                                                            T 63.36                                                                            5.67                                                                             19.71                                                                 F 63.51                                                                            5.66                                                                             19.83                                  XXI  4    2,6-Cl                                                                              N    CH.sub.3                                                                          104-106                                              XXII 4    2,6-CH.sub.3                                                                        N    CH.sub.3                                                                          oil                                                  XXIII                                                                              2    4,6-Cl                                                                              N    CH.sub.3                                                                          115-117                                                                             T 47.43                                                                            4.29                                                                     F 47.68                                                                            4.35                                      XXIV 3    2,6-Br                                                                              N    CH.sub.3                                                 __________________________________________________________________________     *T = theory; F = found.                                                  

In accordance with this invention, it has been found that the compoundsof the present invention are adapted to be employed as fungicidal agentsfor the control of a wide variety of fungal organisms. The compounds areparticularly adapted to be employed for the control of fungal organismsfound on plants, such as, for example, barley powdery mildew (Erysiphegraminis hordeii), grape downy mildew (Plasmopara viticola), wheat rusts(Puccinia sp), verticillium wilt (Verticillium albo-atrum), applepowdery mildew (Podosphaera leucotricha), tobacco black root rot(Thielaviopsis basicola), apple scab (Venturia inaequalis) and othersuch organisms. In such uses, the compounds are usually applied to theaerial portions of plants. The compounds also can be applied in dormantapplications to the woody surfaces of plants or to orchard floorsurfaces for the control of overwintering spores of many fungi. Inaddition, the compounds can be applied to seeds to protect the foliageof the growing plant from attack of fungal organisms such as thosecausing rust or mildew. Furthermore, the compounds can be applied ordistributed in soil for control of fungal organisms that attack seeds orplant roots, particularly those organisms that cause root rot or wilt.

In further operations, the compounds can be included in inks, adhesives,soaps, cutting oils, polymeric materials, oil paints, or latex paints toprevent mold, mildew, or degradation of such materials resulting frommicrobial attack. Additionally, the compounds can be distributed intextile or cellulosic materials, or they can be employed in theimpregnation of wood or lumber to protect such products from fungalorganism which cause rot, mold, mildew, or decay.

It is an advantage of the present invention that compositions containingthe compounds can be applied to vegetation or soil in amounts requiredfor effective control without significant injury to plants. A furtheradvantage is that the compounds exhibit very low mammalian toxicity atthe rates employed for control of fungal organisms. Another advantage isthat a single application of the compounds can provide a residual,extended control of fungi for a period of several months. Also, thecompounds can be effective in eliminating established fungalinfestation. Furthermore, the compounds have been found to betranslocated in plants and thus can provide a systemic protectionagainst fungi that attack plants.

Generally in the actual practice of the method of the present invention,a plant protecting amount of the toxicant compounds can be applied tothe plant by such convenient procedures as soil injection, drenchingwith an aqueous composition, seed treatment, topical spraying, furrowspraying, or other techniques known to those skilled in the art.

The exact dosage of the active toxicant employed can be varied dependingupon the specific plant, disease to be controlled, hardiness of theplant, and the mode of application. Generally, the active ingredientshould be present in an amount equivalent to from about 50 micrograms toabout 125 milligrams or more per plant. Translating this intoconventional application rates, this amount is equivalent to from about0.001 pound to about 2 pounds or more of the active ingredient on a peracre basis (0.0013-2.24 kilogram per hectare), as chemical available tothe plant.

Larger amounts of the active ingredient advantageously may be appliedwhen treatments are employed which distribute the material throughoutthe soil. For example, when the active ingredient is applied as anat-plant row treatment or as an early season post-plant side dresstreatment, those amounts of chemical not proximal to plant roots areessentially unavailable to the plant and therefore not effective as setforth hereinabove. In such practices, amounts of the active ingredientneed to be increased to rates as high as about 10 pounds per acre (11.2kg/hectare) to assure the requisite effective quantity of activeingredient is made available to the plants.

The present invention can be carried out by employing the compoundsdirectly, either singly or in combination. However, the presentinvention also embraces the employment of liquids, dusts, wettablepowders, granules, or encapsulated compositions containing at least oneof said compounds as active ingredient. In such usage, the compound orcompounds can be modified with one or more of a plurality of additamentsor adjuvants including inert solvents, inert liquid carriers, wettingagents and/or surface active dispersing agents and coarsely or finelydivided inert solids. The augmented compositions are also adapted to beemployed as concentrates and subsequently diluted with additional inertcarrier to produce other compositions in the form of dusts, sprays,granules, washes, or drenches. In compositions where the adjuvant is acoarsely or finely divided solid, a surface active agent, or thecombination of a surface active agent and a liquid additament, theadjuvant cooperates with the active component so as to facilitate theinvention. Whether the composition is employed in liquid, wettablepowder, dust, granule, or encapsulated form, the active compound willnormally be present in an amount of from about 2 to 98 percent by weightof the total composition.

In the preparation of dust, or wettable powder compositions, thetoxicant products can be compounded with any of the finely dividedsolids, such as pyrophyllite, talc, chalk, gypsum, fuller's earth,bentonite, attapulgite, starch, casein, gluten, or the like. In suchoperations, the finely divided carrier is ground or mixed with thetoxicant or wet with a solution of the toxicant in a volatile organicsolvent. Also, such compositions when employed as concentrates can bedispersed in water, with or without the aid of dispersing agents to formspray mixtures.

Granular formulations are usually prepared by impregnating a solution ofthe toxicant in a volatile organic solvent onto a bed of coarselydivided attapulgite, bentonite, diatomite, or the like.

Similarly, the toxicant products can be compounded with a suitablewater-immiscible inert organic liquid and a surface active dispersingagent to produce an emulsifiable concentrate which can be furtherdiluted with water and oil to form spray mixtures in the form ofoil-in-water emulsions. In such compositions, the carrier comprises anaqueous emulsion, i.e., a mixture of inert water-immiscible solvent,emulsifying agent, and water. Preferred dispersing agents which can beemployed in these compositions, are oil-soluble materials includingnon-ionic emulsifiers such as the condensation products of alkyleneoxides with the inorganic acids, polyoxyethylene derivatives or sorbitanesters, complex ether alcohols, and the like. Also, oil-soluble ionicemulsifying agents such as mahogany soaps can be used. Suitable inertorganic liquids which can be employed in the compositions includepetroleum oils and distillates, toluene, liquid halohydrocarbons, andsynthetic organic oils. The surface-active dispersing agents are usuallyemployed in liquid compositions and in the amount of from 0.1 to 20percent by weight of the combined weight of the dispersing agent andactive compound.

In addition, other liquid compositions containing the desired amount ofeffective agent can be prepared by dissolving the toxicant in an inertorganic liquid such as acetone, methylene chloride, chlorobenzene, orpetroleum distillates. The preferred inert organic solvent carriers arethose which are adapted to accomplish the penetration and impregnationof the plant and particularly soil with the toxicant compounds and areof such volatility as to leave little permanent residue thereon.Particularly desirable carriers are the petroleum distillates boilingalmost entirely under 400° F. (204° C.) at atmospheric pressure andhaving a flash point above 80° C. The proportion of the compounds ofthis invention employed in a suitable solvent may vary from about 2 toabout 50 percent or higher.

A preferred liquid composition includes the use of the active compoundor compounds in combination with surface active dispersant agents only.In such compositions, it is preferred to use ionic and non-ionic blendsof such dispersant agents in combination with one or more of the activematerials. A particular advantage of such a formulation is thatphytotoxicity associated with certain inert solvents, such as xylene,methylene chloride, or like materials can be avoided. Generally, the useof such formulations will result in compositions containing 75 percentor more of the active component.

Owing to the excellent suspensibility of the above formulation in water,it is convenient and often preferred to prepare and use aqueousconcentrates as stock solutions themselves. In such practices, minoragitation results in a practical, stable formulation very adaptable foruse in its concentrate form to treat soil in sprays or drenches.Additionally, if desired, the concentrates can be easily diluted withadditional water for use as foliar spray treatments, soil drenchtreatments, and the like.

Water miscible organic solvents such as lower alcohols or propyleneglycol can be added to depress the freezing point and further cooperatewith the above system in that they are essentially non-phytotoxic.

The following examples further illustrate the present invention, but, assuch, are not to be construed as limiting in scope.

EXAMPLE XXV

The compound of Example III,1-(5-chloro-2-pyridinyloxy)-3,3-dimethyl-1(1H-1,2,4-triazol-1-yl)-2-butanone,was dissolved in acetone. Aliquots of the solution were diluted withwater to provide dispersions containing 1.6, 6.2, and 25 parts permillion by weight of the test compound (PPM). Tobacco plant seedlingswere transplanted into 2-inch (5 cm) diameter pots containing soilinfested with tobacco black root rot (Thielaviopsis basicola).Immediately after transplanting, the pots were drenched with 40 ml ofsolution, two pots per dilution. Control pots were drenched with acetonesolution containing no test compound. The pots were maintained at atemperature of 60° F. (15.5° C.) and watered daily. The test wasevaluated by estimating the percentage of root system that was injured,the evaluation being made when roots of plants in the control potsshowed 98 percent injury. The plants treated with solution containing1.6 ppm test compound showed 15 percent root injury, and plants treatedwith solutions containing 6.2 and 25 ppm test compound showed no rootinjury.

EXAMPLE XXVI

In two separate series of tests, the foliage of apple tree seedlings wassprayed to run off with solutions of compounds of the invention preparedas described above in Example XXI. Four days after the treatment, theplants were inoculated with spores of Venturia inaequalis. One weekafter the inoculation, the percent control of apple scab disease wasdetermined. The identity of test compound, concentration thereof, andthe results are set forth in Table II.

                  TABLE II                                                        ______________________________________                                                              Percent Control of Venturia                                      Concentration of                                                                           inaequalis at indicated                                 Compound of                                                                            Test Compound                                                                              Concentrations                                          Example No.                                                                            ppm          First Series                                                                              Second Series                               ______________________________________                                        III      19           95           99                                                  75           99          100                                                  300          100         100                                         V        19           75           90                                                  75           99          100                                                  300          100         100                                         VI       19           NT*          97                                                  75           NT           99                                                  300          NT          100                                         VII      19           90          NT                                                   75           99          NT                                                   300          100         NT                                          VIII     19            0          NT                                                   75           95          NT                                                   300          100         NT                                          IX       19           100          95                                                  75           100         100                                                  300          100         100                                         ______________________________________                                         *NT = not tested.                                                        

EXAMPLE XXVII

Three separate series of test were conducted by the procedure describedin Example XXII, except the apple seedlings were inoculated with sporesof Podosphaera leucotricha. The results are set forth in Table III.

                  TABLE III                                                       ______________________________________                                        Compound Concentration                                                                             Percent Control of Podosphaera                           of       of Test     leucotricha                                              Example  Compound    First     Second  Third                                  No.      ppm         Series    Series  Series                                 ______________________________________                                        III      19          50        50      25                                              75          93        93      83                                              300         99        100     100                                    V        19          90        35      75                                              75          97        97      99                                              300         100       100     100                                    VI       19          NT        NT      35                                              75          NT        NT      93                                              300         NT        NT      100                                    VII      19          NT        NT      93                                              75          NT        NT      98                                              300         NT        NT      100                                    VIII     19           0        NT      0                                               75          90        NT      90                                              300         99        NT      100                                    IX       19          83        50      60                                              75          99        95      99                                              300         99        100     100                                    XI       19          NT        NT      25                                              75          NT        NT      75                                              300         NT        NT      100                                    XII      19          NT        NT      25                                              75          NT        NT      98                                              300         NT        NT      100                                    XIV      19          25        NT      0                                               75          50        NT      35                                              300         75        NT      99                                     XVI      19          NT        NT      0                                               75          NT        NT      35                                              300         NT        NT      99                                     XVII     19          NT        NT      0                                               75          NT        NT      35                                              300         NT        NT      97                                     XVIII    19          NT        NT      0                                               75          NT        NT      0                                               300         NT        NT      90                                     ______________________________________                                    

EXAMPLE XXVIII

This example demonstrates the systemic character of compounds of theinvention. Aqueous compositions containing 0.4, 1.6, 6.2 and in someinstances 25 ppm of test compound were prepared as described in ExampleXXI. The compositions were drenched onto soil in which apple plantseedlings were growing. One week later, the plant foliage was sprayedwith a suspension of spores of apple powdery mildew (Podosphaeraleucotricha). When disease symptoms on control plants developed,evaluation of percent control on plants in treated pots was made. Theresults are set forth in Table IV.

                  TABLE IV                                                        ______________________________________                                                  Percent Control of Podosphaera                                      Compound of                                                                             leucotricha at indicated Concentration                              Example No.                                                                             0.4 ppm   1.6 pm    6.2 ppm 25 ppm                                  ______________________________________                                        III       83        99        100     100                                     IV        0         0         25       83                                     V         97        99        100     100                                     VI        75        90        99      100                                     VII       0         25        99       99                                     VIII      97        99        99      100                                     IX        97        100       100     100                                     XI        25        97        99      NT                                      XIII      50        90        99      100                                     XIV       0         0         25       75                                     XVI       0         35        95      100                                     XVII      0         35        100     NT                                      XVIII     0         0         83      NT                                      ______________________________________                                    

What is claimed is:
 1. A substituted1-pyridinyloxy-1-(imidazolyl)-2-butanone compound corresponding to theformula ##STR9## wherein X independently represents halogen, methyl,trichloromethyl, trifluoromethyl, or cyano; n represents an integer of 0to 3; Y represents --CH; and R represents methyl, methoxy, or ethoxy. 2.A compound as defined in claim 1 wherein X is chloro.
 3. A compound asdefined in claim 1 wherein R is methyl.
 4. A fungicidal compositioncomprising as active ingredient a fungicidally effective amount of asubstituted 1-pyridinyloxy-1-(imidazolyl)-2-butanone compoundcorresponding to the formula ##STR10## wherein X independentlyrepresents halogen, methyl, trichloromethyl, trifluoromethyl, or cyano;n represents an integer of 0 to 3; Y represents --CH; and R representsmethyl, methoxy, or ethoxy, in intimate admixture with an inert carriertherefor.
 5. A composition as defined in claim 4 wherein X is chloro. 6.A composition as defined in claim 4 wherein R is methyl.
 7. A method forcontrolling fungi which attack plants which comprises applying toplants, plant parts, or soil a composition containing as the activeingredient, a fungicidally effective amount of a substituted1-pyridinyloxy-1-(imidazolyl)-2-butanone compound corresponding to theformula ##STR11## wherein X independently represents halogen, methyl,trichloromethyl, trifluoromethyl, or cyano; n represents an integer of 0to 3; Y represents --CH; and R represents methyl, methoxy, or ethoxy, inintimate admixture with an inert carrier therefor.
 8. A method asdefined in claim 7 wherein X is chloro.
 9. A method as defined in claim7 wherein R is methyl.
 10. The compound as defined in claim 3 which is1-(6-fluoro-2-pyridinyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanone.11. The compound as defined in claim 3 which is1-(5-cyano-2-pyridinyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanone.12. The composition as defined in claim 6 wherein the compound is1-(6-fluoro-2-pyridinyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanone.13. The composition as defined in claim 6 wherein the compound is1-(5-cyano-2-pyridinyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanone.14. The method as defined in claim 9 wherein the active ingredient is1-(6-fluoro-2-pyridinyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanone.15. The method as defined in claim 9 wherein the active ingredient is1-(5-cyano-2-pyridinyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanone.